We've Had This Conversation Before

July 18, 2026

Lessons From an Educational Time Capsule

“History doesn’t repeat itself, but it often rhymes.” ~ Often attributed to Mark Twain

Every year after ISTE, I spend a little time reflecting. Some years it's a new company that caught my attention. Sometimes it's a leadership conversation that sticks with me on the flight home. Other years it's a product that changes the way I think about where our industry is headed.

This year, it was artificial intelligence, or maybe more accurately, our reaction to it.

Like most people who attended the conference, I couldn't escape it. AI was woven into presentations, product announcements, hallway conversations, and dinner discussions. Depending on who you talked to, artificial intelligence was either the greatest opportunity education has ever seen or the greatest challenge educators would face over the next decade. As I flew home, I found myself asking a simple question: Have we had this conversation before? Not about artificial intelligence itself. About change.

That question sent me down a rabbit hole I wasn't expecting. I spent the last couple weeks searching through old conference programs, keynote speeches, magazine covers, newspaper headlines, and government announcements from the mid-1990s, the same years I was beginning my career in public education. I wasn't looking for nostalgia. I was looking for perspective. Instead, I found something that felt like opening a time capsule.

One of the first things I came across was President Bill Clinton's 1996 State of the Union address. In it, he challenged the nation to connect every classroom in America to what he called the 'Information Superhighway' with computers, quality software, and well-trained teachers. Reading those words nearly thirty years later stopped me in my tracks. Replace the phrase Information Superhighway with artificial intelligence, and much of the speech could easily be mistaken for a session delivered at ISTE this summer.

That same fall, I was walking into my first classroom as a physical education teacher. To be completely honest, I wasn't thinking much about the Information Superhighway. I was trying to survive my first year of teaching. Most classrooms didn't have Internet access. Wi‑Fi didn't exist. If students used computers, they walked to a lab somewhere down the hall, and much of the software they used arrived in a cardboard box on a CD-ROM.

Looking back, I realized something that hadn't occurred to me before: history remembers the speeches. Teachers remember the classrooms.

As I kept reading, the similarities became impossible to ignore. In July of 1997, The Atlantic published 'The Computer Delusion,' questioning whether computers were actually improving teaching and learning. Just a few months later, Time magazine warned that students were using the Internet to download papers and cheat. I couldn't help but smile, not because those concerns weren't real, but because if you replaced one word, Internet with AI, those headlines could have been written this year.

Teachers questioned whether technology would improve learning. Parents worried students would misuse it. School leaders debated training. Policymakers debated adoption. Reading those stories from nearly thirty years ago, I realized we weren't just reading history. We were reading ourselves. Maybe we've always been debating change.

As I continued digging through that time capsule, I began remembering stories from my own career that had very little to do with technology and everything to do with the people using it. For all the attention we give technology, I rarely remember the technology itself. I remember the moments.

One of my favorite memories came when I was an assistant principal. One of the parents at our school was astronaut Frank Culbertson aboard the International Space Station. Through amateur radio operators, Internet connectivity, and a lot of crossed fingers, our students had the opportunity to speak with him while he orbited the Earth. Today we'd schedule a Zoom call without thinking twice. Back then it felt impossible. We duct-taped the cafeteria intercom to a speaker so the entire school could listen. Looking back, I don't remember thinking about the Internet. I remember watching a room full of kids realize they were talking to someone floating above the Earth. Technology made the moment possible, but the moment became a memory. That's true of almost every meaningful technology experience I've had in education.

A few years later when I was a young principal, a SMARTBoard showed up at my school. Nobody explained what it was. I honestly thought it was an expensive whiteboard, and I traded it away. Looking back, that probably wasn't one of my finer technology decisions. Every time I tell that story, people laugh. I laugh too. But underneath the humor is one of the most important leadership lessons I've learned: technology doesn't change education. People do. A SMARTBoard without professional development is expensive furniture. A laptop without thoughtful instruction is simply another device.

As I researched this article, I kept coming back to Seymour Papert. Decades ago he reminded educators that the conversation shouldn't be about computers any more than it should be about pencils. The tool matters only because of what it allows students to create, discover, and understand. Thirty years later, that lesson feels just as relevant. Every generation falls in love with the newest tool. The best educators stay in love with learning.

By 2007 I had become Chief Technology Officer, and our district became one of the earliest in the country to implement Blackboard LMS districtwide. What strikes me isn't Blackboard itself. It's what nobody was debating anymore. The Internet had quietly become infrastructure. We had moved on to better questions: How do we use it well? How do we support teachers? How do we know it's improving learning? That's what history does, it quietly changes the questions.

Somewhere along the way our cameras disappeared. So did our calculators, GPS units, flashlights, music players, and eventually even our wallets. They didn't disappear because they failed. They disappeared because they succeeded. They became so woven into everyday life that we stopped noticing the technology and focused on what it allowed us to do.

As I closed my laptop after several evenings of reading thirty years of speeches, conference programs, magazine covers, and research papers, one observation kept coming back to me. The technologies change, but the cycle doesn't. Every generation begins with extraordinary promises. Those promises give way to skepticism, debates about cheating, concerns over teacher preparation, and bold predictions about the future. Eventually the technology becomes ordinary. It simply becomes part of the work.

Maybe that's why artificial intelligence feels so familiar to me. Not because it's the same as the Internet. It isn't. It's because we've had this conversation before.

I've spent the last thirty years watching education wrestle with transformational change. We've lived through the Internet, interactive whiteboards, one-to-one computing, learning management systems, smartphones, cloud computing, and now AI. Every wave arrived with extraordinary promises. Every wave created anxiety. Every wave forced educators to separate hype from substance while continuing to do what they've always done: help students learn.

That's why I don't think the most important question is whether AI will transform education. History has already answered that. It will. The better question is whether we'll have the wisdom to implement it thoughtfully, the patience to support teachers well, and the discipline to keep learning, not technology, at the center of every decision we make.

Thirty years from now, I doubt educators will attend conference sessions asking whether artificial intelligence belongs in schools. Not because AI won't matter, but because it will. Future educators will be busy debating whatever comes next, convinced they're living through a revolution unlike anything before it. I hope one of them opens a time capsule. I think they'll discover exactly what I did: the technologies will be different, but the conversations will sound remarkably familiar.

History remembers the inventions.

Educators remember the students.